Material-efficient dual role of supporting electrolytes for electro-organic sulfonylation and oxo-functionalization reactions
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Abstract
Transforming conventional chemical processes into more sustainable methods, such as replacing chemical reducing and oxidizing agents, is an attractive target in modern synthetic organic chemistry. Therefore, electro-organic synthesis is taking over an increasingly important aspect of chemical process design. However, many of these processes use indispensable supporting electrolytes merely as charge carriers for electrolyte conductivity. A simultaneous dual role of these as a nucleophilic/electrophilic reagent or an electrochemical mediator increases cost- and material efficiencies and, therefore, represents a resource-saving approach. This dissertation focuses on sustainable reaction development studies using supporting electrolyte salts as a nucleophilic reagent and an electrochemical mediator in a dual role. For instance, sodium sulfinate salts were successfully applied in electrochemical sulfonylation reactions with electron-rich aromatic compounds to form sulfones. Furthermore, nitrate salts were discovered and investigated as electrochemical mediators for oxo-functionalization reactions of cyclic alkanes and alkenes. Demonstrating two different aspects of the supporting electrolyte's dual role as a reagent or mediator is intended to illustrate the great possibilities of broad application areas, which may be of fundamental interest for future electro-organic reaction control.